The rainy season will be upon us before you next read this advice column, so we thought it prudent to remind you that it is Portland, and therefore prudent to wear rubber soles with good traction come October. We’ve been looking for boots whose soles look acceptable for the office, but push the envelope a bit when the pants leg reveals a boot. We landed on these Greeley Chukka’s. The bottom looks like a two-tone oxford, but with some bad-boy uppers to let everyone know you’re the wild card.